Abstract:

Two fully lipidated phosphatidylinositol dimannosides (Ac2PIM2s), (16:0, 16:0)(16:0/16:0)-PIM2 1 containing four palmitoyl residues and (16:0, 18:0)(19:0/16:0)-PIM2 2 containing three different acyl residues were synthesised. They were prepared in 19 steps from DL-1,2:4,5-di-O-isopropylidene-myo-inositol in 1% and 3% yields respectively. Ac2PIM2 2 has a palmitoyl residue at O-6´´ of mannose, a stearoyl residue at O-3 of inositol, and tuberculostearoyl and palmitoyl residues at the sn-1 and sn-2 positions of the phosphatidyl group respectively.